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Jack and Jill and Mom Ch. 02

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Shemale

I put a couple of logs in the fireplace and turned on the gas. Tons of things were going through my mind, not the least of which was trying to determine how far this would go.

A back-rub was innocent enough. But was I actually going to try and put the moves on my mom? And would she be receptive to that? Instead of a scheme that had to play out, everything was sort of out in the open. Mom had caught us, my sister and I, laying in bed exhausted after just having finished an oral exchange.

Caught, Jill then laid out her plan, and mom seemed to take it in stride. Now that I went back over the talk in my mind, she had not consented to anything sexual, but neither had she denied it outright which one might expect. In fact she seemed to have side-stepped around it. Or was that just wishful thinking, that she might actually play along?

The wood started to crackle as the fire caught. I closed the fireplace screen and turned on the stereo to light music. Then I turned down the overhead lights to a dim setting.

Just then Jill came in with drinks. She had a bottle of wine with two wine glasses already filled. Plus a bottle of whiskey and two shot glasses. I looked at her and she back at me. “Just in case anyone needs something stronger,” she said lightly. “Liquid encouragement.”

Mom came in wearing her bath robe. She looked at the tray with drinks, noticing pairs. “Seems like you’re short a glass.”

Jill answered, “Well, I thought this would be enough for the two of you.”

“This is your plan,” mom replied. “I expect service from you too,” she said as she took a glass of wine and took a long pull, eventually finishing in quick order.

“From me?” Jill questioned.

“While Jack gives me a back-massage,” she now dis-robed, revealing a nightie underneath. “You can start on my feet.” She offered the empty glass which Jill now refilled. Mom took it and sat down on the sofa, then put her feet up on the coffee table.

I downed a shot of whiskey. Jill re-filled it, then took the other and took her own shot. I walked around behind the sofa. Jill sat on the low table, next to mom’s feet. We looked at each other. The room was warm from the fire. The ambience was soft and romantic, light music played and firelight flickered on the far wall.

There was a moment of silence, of anticipation, of what might happen.

I looked down from above and behind her, this lovely woman with a slender body in her night-gown, waiting for me. My mom was waiting for me to give her a massage. I gently placed my hands and began to work her neck and shoulders. Her chest exhaled; she must have been holding her breath too.

It could have been a simple backrub, but it was so much more than that. It was erotic and romantic. Time might have slowed, or I was just caught up in it. It wasn’t just that I was touching her skin. I was feeling her essence with my fingers, my hands. I kneaded her shoulders and upper back, to occasional oohs and aahs while Jill worked on her feet and toes.

After about 15 minutes, I leaned over and looked down, noticing the tops of her breasts marsbahis güvenilirmi from my vantage point. I could see her hard nipples pointing out against the sheer fabric of the nightie. I imagined caressing them and squeezing her soft breasts, maybe even while putting her nipple in my mouth, gently biting…

“See something you like,” mom asked. I was caught staring at her chest! Had she seen the look of lust on my face?

But instead of pressing the issue, she changed the topic. “That was lovely, but it’s time for a different position.” She stood, taking another drink from her glass of wine. Then she removed her arms out of the nightie, but still held the fabric to her chest. She laid face-down on the sofa, her bare back exposed. She crossed her arms under her head and rested on them.

“You may resume now,” she instructed.

I walked around the sofa, stopping to take another shot. I leaned down to touch her back. I couldn’t get much pressure and the angle wasn’t right. Mom noticed the dilemma I was trying to solve.

“You can straddle my hips, if the weight is evenly distributed it won’t be too much.”

I gently placed my leg over and sat down on her, with only the sheer nightie between us. I thought I felt her squeeze her buns, and a tingle went through me. But I sure if that was intentional or just a response to my weight.

I tried to focus, so I leaned in and massaged her shoulders again, working on her upper back. “Mmmmm, that’s nice, your hands are so warm,” she cooed. After some time, she gave me more direction. “You can reach my lower back nicely in this position too.”

I worked my hands down and in circular patterns. Occasionally I would gently then firmly use my knuckles to need into her, as I worked into the middle and then lower back.

I got as low on her back as I could, nearly at my own legs. Any more and I would be touching her butt directly. That’s when I thought about it – I was sitting on her, and my groin was the sensory input sending information to my head about her soft, warm ass. I tried to block it out, but that only made me think about it more. I shifted my hips and the feeling of her bum under me made me excited.

I continued the lower back massage, but I was obsessing with her bottom now. Periodically I would move enough to put pressure on her, to angle into her, to rub against her. And periodically she would push back in response. After a few minutes of this, I risked more, and shifted my hips so my penis lined up between her ass cheeks. I leaned in, presumably to reach her shoulders, resulting in me pressing my manhood into her bum through my shorts.

She squeezed her buns again — it was unmistakable this time. And my cock was hard enough to be recognized for what it was. I imagined what it would be like to slide it into her warm pussy, to move in with long strokes, with her ass against my groin. Would it be heaven as I imagined it.

“Seems like someone is enjoying this a little too much,” she replied with a wicked smile. But did she mean her or me? “That’s a different kind of massage,” marsbahis yeni giriş she said as her body shifted and I lifted up, not sure if I had gone too far. She raised to finish her third glass of wine, then laid back down.

“You may use your hands.”

Did she mean just use my hands on her back? Or did she just give permission for me to massage her bum as long as I only used my hands? I was clearly grinding on her, so it seemed vague — was she side stepping the issue, or was it wishful thinking again?

I had to test the theory. I scooted back slightly, off her bottom and sat on her legs, then resumed. She stretched out and I could feel her body relax underneath me. I worked her lower back in a circular pattern. On each pass, I went a couple inches lower. Eventually I was touching her bum, and I decided to stop trying to be accidental about it entirely. Either she would stop it and the massage would be over, or she enjoyed it and I could proceed.

I lifted myself up enough to pull her nightie down further. She lifted her side and allowed me to remove it! She was fully naked now underneath me. I placed my hands on her bottom, softly then firmly as she pushed back and moaned. I kneaded her buns, carefully waiting for any sign that I had gone too far. I scooted back further, now alternating between massaging her legs, her thighs, from the top and sides, then on the inside and up as high as I could still be on her legs. She opened her legs slightly, just enough to permit this amount of massaging. But the response was unmistakable, she was into this and I could continue.

I returned to her bum, grabbing and spreading her cheeks as I worked her bottom with my hands and fingers. I could smell her, and then I reached between her legs and touched her pussy for the first time. It was soft and moist; she was clearly aroused by all this.

“Yes,” she moaned and shifted as I rubbed around her mound. At first I used my hand, my palm, then I inserted a finger into her warmth. She arched, raising up to meet me, inviting me in, then impatiently she pushed back against my hand.

Here was this beautiful woman, a sexy creature, writhing under me. She had needs and I had worked up her body, gradually building and increasing the intensity. I massaged her legs and ass with one hand and fingered her pussy with the other.

“That’s it,” she moaned, “make me come with your hands.”

I was excited, hard and horny. But I resolved to focus my attention on her. I reached down with one hand to grab a cheek and with my thumb rub her clit. With my other I fingered her pussy relentlessly, two fingers then three as I pushed all the way in. My other thumb rested on her asshole, and she began to grunt as she rocked with the motion.

I looked over to see what Jill was doing. She sat quietly in the lounge opposite, her legs spread on the ottoman and she fingered herself while she watched us. When she saw me, she used her fingers and stuck her tongue through, telling me what to do next.

But I didn’t want to leave her out either. I motioned for her to come marsbahis giriş join us on the sofa. She came over and sat down on the other side of me, turning towards us and spreading her legs as she reclined. I reached down and rubbed Jill’s pussy, then managed to get a finger in her pussy. But I didn’t have any angle and couldn’t twist more, so I failed to really finger her strongly. Realizing the limitation, but also that she was so horny and so close, she grabbed my arm with both hands. Now she was rubbing up against my wrist, causing the fingers to move up and down as her pelvic bone grinded on me, controlling the motion of my fingers.

It was hot, and I momentarily released mom so I could finish Jill off with my tongue. Just a few licks and a strong fistful of fingering, and she bucked against me.

“Fuck me, I’m coming!” She cried out, causing mom to look up at us. Jill convulsed and juices squirted from her pussy and onto my hand.

When it was clear she got off, I returned to mom, not wanting to lose the momentum. I lowered my head to her pussy again. I licked lower and lower, eventually reaching her soft bum. I licked her butthole, flicking across the rosebud. Then I spread her ass wide with my alternate hand and stuck my tongue in as far as her ass would allow.

“Oh yes!” She moaned. I fingered her hard, rubbed her clit, and tongue her ass, moving in and out.

“That’s it! You know what I like!” she exclaimed loudly, grabbing the arm rest with both hands as her body tensed and she pushed back against me.

“Your pussy is tight!” I exclaimed between breaths. “But I’ve wanted your ass for so long!” Then I dove back in to lick her butt.

“Finger-fuck me!!” She cried out. “I’m going to come!”

I shoved my face into her pussy now. I licked her clit then inserted my tongue into her pussy alongside my fingers. She squeezed her legs against my head. Her body jolted, white fluid mixing with pussy juice on my fingers and face. She convulsed, and collapsed into the sofa, both relieved and spent.

Softly, I rubbed her back and she lay quietly, face down still. A few minutes passed.

“Mom?” I spoke, breaking the silence.

“I needed that,” she said, raising her body and reaching out to caress my face. “Apparently we both did.” She looked at Jill too. Then she regained herself and found her nightie wedged in the sofa cushion.

“Mom?” I asked, needing some response, some validation.

She stood to leave, “I’m going to take a shower.” She gathered her robe. “Round two starts in 30 minutes.”

“Round two?” Jill asked, sitting up and joining the conversation.

“I know what you want,” she replied. “And you can have everything you want, both of you”. She looked at Jill then back at me. “Three times. That is my price.”

“Wait, both of us?” Jill asked.

“You want something, so does your brother.”

“What?”

“Can’t you tell? Eventually he’s going to want to come too,” she turned, reaching down to grab my crotch through my shorts. “But” she licked her lips, “I’m just not sure where.”

“Mom,” there was no reason to keep it to myself anymore. “There’s so much I want to do to you, with you, for you” I said, reaching out to her. Then I continued, “I don’t know where to begin.”

She looked at my lovingly, “In 30 minutes, I’ll show you.” And with that, she went to shower.

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